(3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

Base Information

Chemical Name:(3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one
CAS No.:79131-71-8
Molecular Formula:C₁₁H₁₅Cl₂NO₅
Molecular Weight:312.15
Hs Code.:

Synonyms:

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Chemical Property of (3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

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Technology Process of (3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

There total 13 articles about (3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 115534-35-5
endo-(+/-)-N-(3-oxo-2-oxabicyclo<3.3.1>non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide

: 78013-07-7,79131-71-8,115649-44-0
(3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / mCPBA / CH₂Cl₂

2: HCOOH, MeOH, Et₃N

3: tetrahydrofuran

4: p-TsOH / dimethylformamide

5: 2,6-lutidine / dimethylformamide / -15 °C

6: 2.) n-Bu₄NF / 1.) THF, 2.) RT

7: CeCl₃ / diethyl ether / -100 °C

8: 90 percent / CrO₃, pyr / CH₂Cl₂

9: 80 percent / Et₃N, 4-pyrrolidinopyridine

10: 70 percent / NaOMe / methanol

11: 1.) n-Bu₄NF, 2.) HCl / 1.) THF, 52 deg C, 2.) MeOH

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; methanol; formic acid; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00252a060

Reference yield:

: 115534-36-6,115648-42-5
2-Trimethylsilanyl-ethanesulfonic acid ((1R,6R,9R)-8-oxo-3,7-dioxa-tricyclo[4.3.1.0^2,4]dec-9-yl)-amide

: 78013-07-7,79131-71-8,115649-44-0
(3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

Guidance literature:: Multi-step reaction with 10 steps

1: HCOOH, MeOH, Et₃N

2: tetrahydrofuran

3: p-TsOH / dimethylformamide

4: 2,6-lutidine / dimethylformamide / -15 °C

5: 2.) n-Bu₄NF / 1.) THF, 2.) RT

6: CeCl₃ / diethyl ether / -100 °C

7: 90 percent / CrO₃, pyr / CH₂Cl₂

8: 80 percent / Et₃N, 4-pyrrolidinopyridine

9: 70 percent / NaOMe / methanol

10: 1.) n-Bu₄NF, 2.) HCl / 1.) THF, 52 deg C, 2.) MeOH

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; methanol; formic acid; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00252a060

Reference yield:

: 115534-37-7
2-Trimethylsilanyl-ethanesulfonic acid ((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl)-amide

: 78013-07-7,79131-71-8,115649-44-0
(3R,4S,4aS,5S,6S)-4-Amino-3-dichloromethyl-5,6,8-trihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one

Guidance literature:: Multi-step reaction with 9 steps

1: tetrahydrofuran

2: p-TsOH / dimethylformamide

3: 2,6-lutidine / dimethylformamide / -15 °C

4: 2.) n-Bu₄NF / 1.) THF, 2.) RT

5: CeCl₃ / diethyl ether / -100 °C

6: 90 percent / CrO₃, pyr / CH₂Cl₂

7: 80 percent / Et₃N, 4-pyrrolidinopyridine

8: 70 percent / NaOMe / methanol

9: 1.) n-Bu₄NF, 2.) HCl / 1.) THF, 52 deg C, 2.) MeOH

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00252a060